Synthesis of Novel Schiff Base and Azetidinone Derivatives ...downloads.hindawi.com/journals/jchem/2004/158924.pdf · 2 Warad D U Satish C D, Kulkarni V H and Bajgur C S, Indian J

E-Journal of Chemistry Vol. 1, No. 5, pp 272-276, October 2004

http://www.e-journal.home-page.org

SySynthesis of Novel Schiff Bnthesis of Novel Schiff Basease and Azetidinone and Azetidinone

DDerivatives and their Antibacterial erivatives and their Antibacterial AActivityctivity

KAMAL VASHI and H. B. NAIK

Department of Chemistry, Veer Narmad South Gujarat University,

Surat 395007, India.

Received 20 September 2004; Accepted 10 October 2004

AbstractAbstract A series of Compound 4-(2’-hydroxy-3’-chloro-5’-ethyl phen-1’-yl)-1-(4’-tolyl)-3-chloro-2-azetidinone 44aa--jj have been prepared by the reaction of 2� -hydroxy-3� -chloro-5� -ethyl-N-(p-tolyl)-chalconimines 33aa--j j with chloroacetyl chloride in the presence of triethylamine. The Schiff base derivatives 33aa--jj has been prepared by the condensation of different substituted chalone derivatives 11 with p-toluidine 22.. The synthesized compounds were screened for their antibacterial activity against Staphylococcus aureus and Escherichia coli.

Key wordsKey words Synthesis, Chalcone, Schiff Base, 2-Azetidinone, Antibacterial activity.

IntroductionIntroduction

Schiff base has good antimicrobial, fungicidal1 and pharmacological applications2 and it can be prepared by the acid catalyzed reaction of amines & ketones or aldehydes. 2-Azetidinone derivatives have been reported to possess antitubercular3, antibacterial4, antidegenerative, fungicidal5 and antibiotic6 activity. Experimental section All the melting points were determined in open capillaries and are uncorrected. The purity of compounds was checked by TLC on silica gel ‘G’ coated glass plates. IR spectra were recorded with KBr on Shimadzu FT-IR 8300 spectrophotometer, 1H NMR spectra on a Brucker DRX - 300 in CDCl3 at 200 MHz using TMS as an internal standard. Synthesis of 2� -hydroxy-3’-chloro-5’-ethyl-N-(p-tolyl)-chalconimines. (3) In a 250 ml R. B. F. mixture of substituted chalcone derivative 1 (0.01 mole) and p-toluidine 2 (0.01 mole) were taken. About 20 ml methanol was added to it and refluxed for 5 - 6 hrs. After the completion of reaction, the solvent was removed by vacuum distillation. The solid product was filtered, dried and recrystallised from absolute alcohol. All substituted Schiff bases were prepared in the similar manner. Their characterization data are shown in TableTable -- I I. Synthesis of 4-(2’-hydroxy-3’-chloro-5’-ethyl phen-1’-yl)-1-(4’-tolyl)-3-chloro-2-azetidinone (4) A mixture of 2’-hydroxy-3’-chloro-5’-ethyl-N-(p-tolyl)-chalconimines 3 (0.01mole) in benzene was taken in a 50 ml round bottom flask. To it chloroacetyl chloride (0.01 mole), triethylamine (0.01 mole) in benzene were added slowly. It was refluxed for 15 - 16 hrs. The triethylamine hydrochloride formed during the reaction, was removed and the benzene was distilled off to get the product. The crude product obtained was recrystallised from ethanol. Other azetidinone derivatives were prepared in the similar manner. Their characterization data are shown in TableTable -- IIII.

N

CH CH

CH3

OH

Cl

Et

Cl

O

Cl

Et

OH

C CH CH

N

CH3

Cl

Et

OH

C CH CH

O

+

NH2

CH3

R

5 - 6 hrs.Methanol

ClCH2COCl

TEA15 - 16 hrs

R

R

273 KAMAL VASHI et al.

SSCHEMECHEME

1 2

3a-j

4a-j

Where, RR = p-H, p-Cl, 2,4-(Cl)2, o-OH, p-OH, p-CH3, m-NO2, o-OCH3, p-OCH3, p-N(CH3)2

Synthesis of Novel Schiff Base and Antibacterial Activity 274

TABLE – I CHARACTERIZATION DATA OF COMPOUNDS 3a-j % Analysis Calc.(Found) No. R M.F.

(M.W.) Yield (%)

M.P. (0C)

C H N

3a p-H C24H22NOCl (375.89)

80 83 76.69 (76.62)

5.90 (5.96)

3.73 (3.77)

3b p-Cl C24H21NOCl2

(410.33) 77 112 70.25

(70.29) 5.16 (5.22)

3.41 (3.47)

3c 2,4-(Cl)2 C24H20NOCl3

(444.78) 75 96 64.81 (64.87)

4.53 (4.58)

3.15 (3.19)

3d o-OH C24H22NO2Cl (391.89)

76 107 73.56 (73.51)

5.66 (5.73)

3.57 (3.52)

3e p-OH C24H22NO2Cl (391.89)

72 98 73.56 (73.60)

5.66 (5.71)

3.57 (3.62)

3f p-CH3 C25H24NOCl

(389.91) 77 88 77.01 (77.08)

6.20 (6.26)

3.59 (3.52)

3g m-NO2 C24H21N2O3Cl

(420.88) 68 119 68.49

(68.44) 5.03 (5.09)

6.66 (6.71)

3h o-OCH3 C25H24NO2Cl

(405.91) 73 114 73.97

(73.91) 5.96 (5.92)

3.45 (3.41)

3i p-OCH3 C25H24NO2Cl

(405.91) 70 91 73.97

(73.92) 5.96 (5.99)

3.45 (3.49)

3j p-N(CH3)2 C26H27N2OCl

(418.95) 71 102 74.54 (74.60)

6.50 (6.57)

6.69 (6.74)

TABLE TABLE –– IIII CHARACTERIZATION DATA OF COMPOUNDS 4a-j

% Analysis Calc.(Found) No. R M.F.

(M.W.) Yield (%)

M.P. (0C)

C H N

4a p-H C26H23NO2Cl2

(452.37) 65 121 69.03

(69.08) 5.12 (5.16)

3.10 (3.15)

4b p-Cl C26H22NO2Cl3

(486.81) 60 134 64.15 (64.20)

4.56 (4.52)

2.88 (2.85)

4c 2,4-(Cl)2 C26H21NO2Cl4

(521.26) 62 127 59.91

(59.97) 4.06 (4.01)

2.69 (2.72)

4d o-OH C26H23NO3Cl2

(468.37) 60 118 66.67

(66.62) 4.95 (4.92)

2.99 (2.94)

4e p-OH C26H23NO3Cl2

(468.37) 60 142 66.67 (66.61)

4.95 (4.99)

2.99 (2.92)

4f p-CH3 C27H25NO2Cl2

(466.39) 62 157 69.53

(69.58) 5.40 (5.45)

3.00 (3.06)

4g m-NO2 C26H22N2O4Cl2

(497.36) 65 158 62.79

(62.84) 4.46 (4.51)

5.63 (5.68)

4h o-OCH3 C27H25NO3Cl2

(482.39) 58 137 67.22 (67.27)

5.22 (5.24)

2.90 (2.93)

4i p-OCH3 C27H25NO3Cl2

(482.39) 55 129 67.22

(67.25) 5.22 (5.26)

2.90 (2.95)

4j p-N(CH3)2 C28H28N2O2Cl2

(495.44) 65 149 67.88

(67.91) 5.70 (5.75)

5.65 (5.69)

275 KAMAL VASHI et al. Results and Results and DDiscussioniscussion Structures of the compounds synthesized have been confirmed by elemental analysis, IR spectra and 1H NMR spectra. 2-Azetidinone compound shows IR absorption bands at 1330-1310 cm-1 (Ar-CH3), 1720-1700 cm-1 (C=O stretching) and 1360-1310 cm-1 (C-N stretching), 1637 (CH=CH stretching), 1712 (C=O stretching), 3037 (-OH stretching). 1H NMR of compound 4: ä 2.25 (3H, s, Ar-CH3), 3.45 (3H, s, -CH), 9.2 (1H, s, -OH), 6.95 - 7.37 (9H, m, Ar-H).

Antibacterial activity The synthesized compounds were tested for their antibacterial activity by measuring the inhibition area on agar plates (diffusimetric method)7 with Staphylococcus aureus and Escherichia coli as test germs. TABLETABLE –– III III ANTIBACTERIAL ACTIVITY OF NEWLY SYNTHESISED COMPOUNDS, ZONE OF INHIBITION (mm)

No. S. aureus. E. coli. No. S. aureus. E. coli. 3a 12.0 9.0 4a 12.0 8.0 3b 11.0 10.0 4b 10.0 11.0 3c 9.0 8.0 4c 9.0 7.0 3d 8.0 11.0 4d 7.0 12.0 3e 8.0 10.0 4e 9.0 11.0 3f 9.0 7.0 4f 11.0 7.0 3g 10.0 11.0 4g 8.0 12.0 3h 11.0 10.0 4h 12.0 9.0 3i 7.0 8.0 4i 7.0 10.0 3j 9.0 12.0 4j 10.0 12.0

Acknowledgement The authors are thankful to The Head, Department of Chemistry, Veer Narmad South Gujarat University, Surat for providing research facilities and CDRI, Lucknow for providing 1H NMR spectra. ReferencesReferences 1 Dash B, Mahapatra P K , Panda D and Patnaik J M, J. Indian Chem. Soc, 1984, 6161, 1061. 2 Warad D U Satish C D, Kulkarni V H and Bajgur C S, Indian J. Chem, 2000, 39A,39A, 415. 3 Desai P S and Desai K R, J. Indian Chem Soc, 1994, 7171, 155. 4 Fadayon M, Kulkarni V D and Pakdaman,A S H, Asian J. Chem, 1993, 5(2)5(2), 282. 5 Giri S and Khan M, J. Indian Chem. Soc, 1994, 7171, 201. 6 Akiba K and Wada M, Chem Abstr, 1989, 111111, 96964b. 7 Weber A D and Sanders C S, Antimicrob Agents Chemother, 1990, 3434, 156.

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Synthesis of Novel Schiff Base and Azetidinone Derivatives ...downloads.hindawi.com/journals/jchem/2004/158924.pdf · 2 Warad D U Satish C D, Kulkarni V H and Bajgur C S, Indian J